Your Ultimate Guide to Real Estate on Chicago's North Shore


Hubbard Woods in Winnetka, ILphoto: Don Bishop

Winnetka is one of the North Shore’s most charming villages.  Located approximately 17 miles from downtown Chicago, Winnetka lies just north of Wilmette and south of Glencoe. With a population of 12,419, Winnetka is the third smallest community on the North Shore, but one of the most affluent. It was named one of the “best places to live”  and one of the top 25 highest earning towns in America by CNN Money in 2009.


Housing stock in Winnetka is comprised mostly of single family homes, but there are condominium buildings and townhomes scattered throughout the village. Typical housing styles are traditional: colonials, Tudors, Victorians and 4-squares of brick, stucco and lap siding. Houses on the east side of Green Bay Road tend to be larger than those on the west side. There are gorgeous mansions all along Sheridan Road, many with frontage on Lake Michigan. As there is little vacant land in Winnetka, any new construction is infill from tear-downs of older, smaller homes.

Housing prices in Winnetka range from $450,000 to over $10,000, 000, with a median price of $700,000. The mansions along the lake command prices of up to $10,000,000.

If you would like information about homes for sale in Winnetka, go here. Or call me at 847-687-5957 if you would like to see one (or more) of them. I’d be happy to help you!


Like most North Shore communities, Winnetka has excellent public schools. There are three elementary schools in District 36: Crow Island, Hubbard Woods and Greeley. The Skokie School serves 5th and 6th grades and Washburne School serves 7th and 8th grades. High schoolers attend New Trier High School, which has long been recognized as one of the top high schools in the country.  9th graders go to the Northfield campus and upper classmen attend the Winnetka campus.

There are also private and parochial schools in the area: North Shore Country Day School is a private K-12 academy. Faith, Hope & Charity and Sacred Heart are Catholic schools serving grades JK-8. Loyola Academy, in Wilmette, is a Catholic high school. The Hadley School for the Blind is also located in Winnetka.


Winnetka ‘s Park District offers a wide array of activities. There are three beaches for swimming (Maple St., Elder St. and Tower Road beaches), one for boating and sailing (Lloyd Beach) and one that allows dogs on leashes (Centennial Park). The A.C. Nielsen Tennis Center on Hibbard Road has 8 indoor and 12 outdoor tennis courts and offers clinics, lessons and league programs. The Winnetka Golf Club has an 18 hole public course as well as a par 3 course. The Winnetka Ice Arena offers figure skating and hockey.Paddle tennis is also popular in Winnetka and the Wiinetka Platform tennis Center hosts leagues all winter.

The village is bounded on the west by the Skokie Lagoons and the Forest Preserve, which runs north and south with walking and riding trails.


The Union Pacific Metra train goes south to the Ogilvy Transportation Center in downtown Chicago and north to Waukegan. There are three stops in Winnetka: Indian Hill,  Winnetka and Hubbard Woods. The village is also served by the PACE suburban bus system. Those who prefer to drive downtown can hop on the Edens Expressway at Willow Road.

Fun Facts

Winnetka is the home town of Conor Dwyer, 2012 Olympic Gold Medal winner in the men’s 4 x 200 free relay.

Several movies (or portions thereof) have been shot in Winnetka over the years, including Home Alone, Sixteen Candles, Ferris Bueller’s Day Off, Breakfast Club and Ocean’s 12.

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